Skipwith Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Your Skipwith Vacation

Skip the hassle of planning your next exciting adventure with a Skipwith vacation package. Whether you're lured here by its food, history, art or other highlights, this city offers countless exciting experiences to delve into. There's plenty to add to your itinerary during your trip to Skipwith, beginning with popular sights such as Parker Sydnor Cabin and Prestwould Plantation. Browse Expedia's wide range of travel options and start organizing your ideal vacation to Skipwith now.

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Skipwith Hotel Deals

Super 8 by Wyndham South Boston VA

Super 8 by Wyndham South Boston VA

2 out of 5
1040 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $77 total per night from Nov 30 to Dec 1
$77 total
Nov 30 - Dec 1
Total with taxes and fees
6.8/10 (455 reviews)
Great ataff.Best hotel to stay at on that side of town.

Reviewed on Nov 6, 2025

Super 8 by Wyndham South Boston VA
Clarion Pointe South Boston - Danville East

Clarion Pointe South Boston - Danville East

3.5 out of 5
1074 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $90 total per night from Nov 28 to Nov 29
$90 total
Nov 28 - Nov 29
Total with taxes and fees
7/10 Good! (284 reviews)
Staff

Reviewed on Nov 12, 2025

Clarion Pointe South Boston - Danville East
Clarion Pointe on the lake Clarksville-South Hill West

Clarion Pointe on the lake Clarksville-South Hill West

2.5 out of 5
103 2nd St Clarksville VA
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $111 total per night from Nov 23 to Nov 24
$111 total
Nov 23 - Nov 24
Total with taxes and fees
7.8/10 Good! (256 reviews)
The stay here is always pleasant. The staff is always, always nice when i come. If i need anything they fix the problem fast. Can't wait to stay again

Reviewed on Nov 19, 2025

Clarion Pointe on the lake Clarksville-South Hill West
See all 111 properties in Skipwith
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Skipwith Vacation Packages

Skipwith Essential Information

Language
English
Currency
U.S dollars
Top Sights
Occoneechee State Park, Staunton River State Park and Clarksville Regional Museum

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Frequently asked questions

How much does a Skipwith vacation package cost?
You can snap up a vacation package to this destination on Expedia. But how much your vacation to Skipwith costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Skipwith?
If you'd like to score a cheap Skipwith vacation package, consider planning a trip in November, December and January. You'll typically find lower rates on hotels and flights during these months — ideal for a budget-friendly break.
How many days is enough for Skipwith?
The ideal length for your Skipwith vacation depends on what you'd like to see. Usually, a few days to a week will give you enough time to tick off all the top sights and discover some hidden treasures along the way.
How to find the best Skipwith package deals?
Use Expedia's filter tool to find some great Skipwith package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Skipwith package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Skipwith vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still get the freedom to create a customized Skipwith vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Skipwith?
If you're considering a spontaneous Skipwith getaway, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Skipwith vacation packages?
If you're like us, you love traveling but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Skipwith vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.